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Hotels in Windward Cay, Orlando

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5

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Star rating

Our top choices for Windward Cay hotels

Exterior

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport
4.0 star property
21.3 km from Windward Cay
9.4 out of 10, Exceptional, (4,230 reviews)
"great stay , convenient location"
United States
RICHARD
The price is CA $239
CA $269 total
includes taxes & fees
Jun 24 - Jun 25
Hyatt Regency Orlando International Airport
Lobby

Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport
3.5 star property
23.4 km from Windward Cay
9.0 out of 10, Wonderful, (2,501 reviews)
"Friendly staff, breakfast was excellent!"
Canada
Roger
The price is CA $119
CA $134 total
includes taxes & fees
Jul 5 - Jul 6
Fairfield Inn By Marriott Orlando Airport
Free daily buffet breakfast

Hampton Inn Orlando-International Airport

Hampton Inn Orlando-International Airport
2.5 star property
23.3 km from Windward Cay
9.0 out of 10, Wonderful, (1,985 reviews)
"Great stay."
United States
John
The price is CA $121
CA $136 total
includes taxes & fees
Jul 6 - Jul 7
Hampton Inn Orlando-International Airport
Property amenity

Staybridge Suites Orlando Airport South by IHG

Staybridge Suites Orlando Airport South by IHG
3.0 star property
23 km from Windward Cay
9.0 out of 10, Wonderful, (2,046 reviews)
"Great stay, very good breakfast"
United States
Tara
The price is CA $125
CA $140 total
includes taxes & fees
Jun 29 - Jun 30
Staybridge Suites Orlando Airport South by IHG
Restaurant

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
23.4 km from Windward Cay
8.8 out of 10, Excellent, (4,013 reviews)
"The breakfast was really good and check in was a breeze, Very friendly staff."
United States
Patrinella
The price is CA $116
CA $130 total
includes taxes & fees
Jun 22 - Jun 23
Wingate by Wyndham - Orlando International Airport
Studio Suite, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Accessible)

Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport
3.0 star property
22.9 km from Windward Cay
8.2 out of 10, Very good, (5,876 reviews)
"Amazing loved this place"
United States
Kareisha Grant
The price is CA $126
CA $142 total
includes taxes & fees
Jul 13 - Jul 14
Ramada by Wyndham Suites Orlando Airport
Interior detail

Holiday Inn Orlando International Airport by IHG

Holiday Inn Orlando International Airport by IHG
3.5 star property
23.2 km from Windward Cay
8.4 out of 10, Very good, (1,538 reviews)
"Great location to the airport and places to eat/shop"
United States
leon
The price is CA $137
CA $154 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Orlando International Airport by IHG
Terrace/patio

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
22.7 km from Windward Cay
9.6 out of 10, Exceptional, (2,953 reviews)
"Nice place to stay"
United States
LaToya
The price is CA $164
CA $185 total
includes taxes & fees
Jul 5 - Jul 6
Hyatt House Orlando Airport
Exterior

DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport
4.0 star property
23.2 km from Windward Cay
8.8 out of 10, Excellent, (2,429 reviews)
"Airport shuttle and location were great!"
United States
Kimberly
The price is CA $117
CA $131 total
includes taxes & fees
Jun 28 - Jun 29
DoubleTree by Hilton Orlando Airport
Premium bedding, pillowtop beds, in-room safe, desk

Hyatt Place Orlando Airport

Hyatt Place Orlando Airport
3.0 star property
22.9 km from Windward Cay
9.0 out of 10, Wonderful, (1,768 reviews)
"Hotel staff were very helpful and the hotel was clean."
United States
Stacey
The price is CA $144
CA $162 total
includes taxes & fees
Jun 23 - Jun 24
Hyatt Place Orlando Airport
Exterior

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
3.0 star property
22.8 km from Windward Cay
7.4 out of 10, Good, (2,176 reviews)
"great price for the stay and location"
United States
Robert
The price is CA $106
CA $119 total
includes taxes & fees
Jul 21 - Jul 22
La Quinta Inn & Suites by Wyndham Orlando Airport
Lobby

Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL
3.0 star property
22.8 km from Windward Cay
8.0 out of 10, Very good, (4,643 reviews)
"Clean rooms and great breakfast"
United States
Rebecca
The price is CA $113
CA $127 total
includes taxes & fees
Jul 14 - Jul 15
Country Inn & Suites by Radisson, Orlando Airport, FL
Exterior

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
22.8 km from Windward Cay
9.4 out of 10, Exceptional, (2,730 reviews)
"Great stay."
United States
Jose
The price is CA $138
CA $155 total
includes taxes & fees
Jun 28 - Jun 29
Hampton Inn & Suites Orlando Airport @ Gateway Village
Exterior

EVEN Hotel Orlando International Airport by IHG

EVEN Hotel Orlando International Airport by IHG
3.5 star property
21.2 km from Windward Cay
9.4 out of 10, Exceptional, (566 reviews)
"Great location!"
United States
Mark
The price is CA $126
CA $142 total
includes taxes & fees
Jul 20 - Jul 21
EVEN Hotel Orlando International Airport by IHG
Exterior

avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG
2.5 star property
21.2 km from Windward Cay
9.2 out of 10, Wonderful, (2,216 reviews)
"Great, easy convenient place to stay."
United States
Jacob
The price is CA $125
CA $140 total
includes taxes & fees
Jul 20 - Jul 21
avid hotel Orlando International Airport by IHG
Lobby

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
21.1 km from Windward Cay
8.8 out of 10, Excellent, (1,903 reviews)
"The room was very spacious and clean! Great location by airport!"
United States
Hector
The price is CA $131
CA $148 total
includes taxes & fees
Jul 13 - Jul 14
Cambria Hotel Orlando Airport
Fitness facility

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
19.9 km from Windward Cay
9.0 out of 10, Wonderful, (4,048 reviews)
"Good hotel near the airport"
United States
Brandon
The price is CA $113
CA $127 total
includes taxes & fees
Jun 21 - Jun 22
Wyndham Garden Orlando Airport
Lobby

Sleep Inn & Suites Orlando International Airport

Sleep Inn & Suites Orlando International Airport
2.5 star property
19.4 km from Windward Cay
8.0 out of 10, Very good, (1,573 reviews)
"Overall good stay"
United States
Nakia
The price is CA $86
CA $97 total
includes taxes & fees
Jun 30 - Jul 1
Sleep Inn & Suites Orlando International Airport
Terrace/patio

The Delaney Hotel

The Delaney Hotel
3.5 star property
25.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,123 reviews)
"Excellent hotel!"
United States
Jeffrey
The price is CA $188
CA $211 total
includes taxes & fees
Jun 28 - Jun 29
The Delaney Hotel
Reception

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
16.9 km from Windward Cay
9.2 out of 10, Wonderful, (1,370 reviews)
"Hotel was excellent employees are very nice"
United States
Dawn
The price is CA $239
CA $305 total
includes taxes & fees
Jul 13 - Jul 14
Florida Hotel & Conference Center in the Florida Mall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.
A golf course with bunkers, water hazards, and a large lake.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.
Photo by Gary Burke
Open Photo by Gary Burke

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.
A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Top Windward Cay Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

8/10 Good
"Room and property were well maintained and clean. Staff was friendly and helpful. However I will note that they should be more aware of the activities happening at the property. We tried going to the pool and quickly had to leave because there were guests blaring inappropriate music and dancing inappropriately for a family environment. While I understand they can’t prevent how guests act and it could have been a one time instance, I wish they handled the situation differently after multiple complaints from guests."
Andrew 3-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

Frequently asked questions

What's it like in Windward Cay?
Travelers to the Windward Cay neighborhood in Kissimmee will be sure to enjoy their stay.
How many hotels will I find in Windward Cay?
Expedia has 33 hotels and other accommodations in Windward Cay to choose from, making this an ideal home base for exploring the greater Kissimmee area.
If I need to cancel my hotel reservation in Windward Cay, will I receive a refund?
Yes, most hotel reservations are refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Windward Cay.
What is there to do around this Kissimmee neighborhood?
A few places to visit in the area around Windward Cay include Old Town, Medieval Times, and Kissimmee Go-Karts. While you're out sightseeing, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.

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